Winsted, CT 55+ active adult communities & homes for sale

79 communities near Winsted

Sort by:

Relevance

3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

The Village at Oxford Gre...

$400ks - $500ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Pond Spring Village

$300ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

Stoneleigh Woods at Carme...

$400ks

Stoneleigh Woods at Carme..., Carmel, NY

Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

The Village at Whispering...

$400ks

The Village at Whispering...Rotterdam, NY

New Construction | 55+ age-restricted | Built 2025 - present | 85 homes

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Glassbury Court at Cold S...

$500ks - $700ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

Castle Heights of Cheshir...

$500ks - $600ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

North Woods of Colchester

$300ks - $400ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

RiverWalk

$500ks - $600ks

RiverWalk, Branford, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes

5 rating (3 reviews)

Founders Ridge

$300ks - $400ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

77 Sunset Lane

$400ks - $700ks

77 Sunset Lane, Ridgefield, CT

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes

Bartlett Hollow

$200ks - $400ks

Bartlett Hollow, Middletown, CT

New Construction | 55+ age-restricted | Built 2015 - present | 25 homes

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

Boulder Brook

$200ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Gloria Commons

$200ks - $300ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

Long Hill Village

$300ks - $400ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

1...2

New Heritage Village

581 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$350,000

2 beds

2 baths

1,398 sq ft

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488

383 SEQUOIA LN B, STRATFORD, CT, 06614

19 PLUMROSE CT 19, PORTLAND, CT, 06480

Community: Bartlett Hill

New Heritage Village

38 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$299,900

2 beds

2 baths

1,032 sq ft

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$450,000

1 beds

2 baths

1,360 sq ft

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614

Community: Oronoque Village

New Baldwin Station

15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461

$599,000

2 beds

3 baths

2,331 sq ft

Condo

15 JASMINE CIR 15, MILFORD, CT, 06461

Community: Baldwin Station

New The Village at Oxford Greens

941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Fairview at Oxford Greens

$699,900

2 beds

2 baths

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478

Community: Fairview at Oxford Greens

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

New Rivington

64 WARRINGTON ROUND 64, DANBURY, CT, 068..., Danbury, CT 06810

$649,900

3 beds

3 baths

1,600 sq ft

Condo

64 WARRINGTON ROUND 64, DANBURY, CT, 068...

Community: Rivington

New The Gardens of Wilbraham

79 CHERRY DR 79, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$435,000

2 beds

2 baths

1,376 sq ft

Condo

79 CHERRY DR 79, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

Regency at Wappinger

36 FARMINGTON RD, WAPPINGER, NY, 12590, Wappinger, NY 12590

$750,000

2 beds

3 baths

2,600 sq ft

House

36 FARMINGTON RD, WAPPINGER, NY, 12590

Community: Regency at Wappinger

Heritage Village

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$518,000

3 beds

2 baths

1,716 sq ft

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...

Community: Heritage Village

Jefferson Village

18 HASTINGS CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$349,000

1 beds

1 baths

850 sq ft

Condo

18 HASTINGS CT B, YORKTOWN, NY, 10598

Community: Jefferson Village

Heritage Village

76 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$249,000

2 beds

2 baths

1,308 sq ft

Condo

76 HERITAGE VLG C, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

773 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$255,000

2 beds

2 baths

1,071 sq ft

Condo

773 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Hills

358 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$620,000

2 beds

3 baths

1,550 sq ft

Condo

358 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Newtown Woods

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470, Newtown, CT 06470

$595,000

2 beds

2 baths

1,747 sq ft

Condo

232 BROOKSIDE CT 232, NEWTOWN, CT, 06470

Community: Newtown Woods

Glassbury Court at Cold Spring

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051..., Philipstown, NY 10516

$698,000

2 beds

2 baths

1,974 sq ft

Condo

10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051...

Community: Glassbury Court at Cold Spring

Heritage Village

818 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$449,000

2 beds

2 baths

1,432 sq ft

Condo

818 HERITAGE VLG B, SOUTHBURY, CT, 06488

46 BUCKSKIN LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Heritage Hills

$450,000

1 beds

1 baths

955 sq ft

Condo

128 HERITAGE HILLS DR B, SOMERS, NY, 105...

Community: Heritage Hills

Heritage Hills

156 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$649,000

3 beds

2 baths

1,689 sq ft

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Frequently Asked Questions

What size 55+ communities are there in Winsted?

In Winsted, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winsted?

The smallest 55+ community in Winsted has 38 homes, the largest has 38 homes, and the average community consists of 38 homes.

Are there gated 55+ communities in Winsted?

No, there are no gated 55+ communities in Winsted.

Want more information about active adult communities around Winsted?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Winsted?

Call us: (860) 909-8066

79 communities

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Jul 21, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Winsted, CT 55+ active adult communities & homes for sale

79 communities near Winsted

166 homes near Winsted

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

970 sq ft

Condo

2 beds

2 baths

1,296 sq ft

Condo

1 beds

2 baths

1,426 sq ft

Condo

1 beds

3 baths

1,360 sq ft

Condo

2 beds

2 baths

1,974 sq ft

House

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,205 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

3 baths

1,503 sq ft

2 beds

2 baths

1,032 sq ft

Condo

1 beds

2 baths

1,360 sq ft

Condo

2 beds

3 baths

2,331 sq ft

Condo

2 beds

2 baths

1,682 sq ft

2 beds

2 baths

1,682 sq ft

3 beds

3 baths

1,600 sq ft

Condo

2 beds

2 baths

1,376 sq ft

Condo

2 beds

3 baths

2,600 sq ft

House

3 beds

2 baths

1,716 sq ft

Condo